Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen

Wolny, Anna; Siewniak, Agnieszka; Zdarta, Jakub; Ciesielczyk, Filip; Latos, Piotr; Jurczyk, Sebastian; Nghiem, Long D.; Jesionowski, Teofil; Chrobok, Anna

doi:10.1016/j.eti.2022.102936

Cited by 9 publications

(2 citation statements)

References 53 publications

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“…The concept of supported ionic liquid phases (SILPs) describes materials where a thin layer of ionic liquid remains confined on a porous solid support, resulting in composite materials that possess unique properties . The combination of the liquid-like behavior of ionic liquids with the structural integrity of solid supports lead to numerous applications that have emerged over the past years, covering catalysis, − gas purification, and storage, − as well as metal recovery. − Especially in catalysis, SILPs combine the properties of ionic liquids with the advantages of heterogeneous systems, such as easy catalyst separation and improved mass transfer. Furthermore, the application of SILPs circumvents the use of bulk quantities of ionic liquids, which is not feasible for their application on an industrial scale. − …”

Section: Introductionmentioning

confidence: 99%

Silicon Oxycarbide (SiOC)-Supported Ionic Liquids: Heterogeneous Catalysts for Cyclic Carbonate Formation

Mikšovsky,

Rauchenwald,

Naghdi

et al. 2024

ACS Sustainable Chem. Eng.

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Silicon oxycarbides (SiOCs) impregnated with tetrabutylammonium halides (TBAX) were investigated as an alternative to silica-based supported ionic liquid phases for the production of bio-based cyclic carbonates derived from limonene and linseed oil. The support materials and the supported ionic liquid phases (SILPs) were characterized via Fourier transform infrared spectroscopy, thermogravimetric analysis, nitrogen adsorption, X-ray photoelectron spectroscopy, microscopy, and solvent adsorption. The silicon oxycarbide supports were pyrolyzed at 300−900 °C prior to being coated with different tetrabutylammonium halides and further used as heterogeneous catalysts for the formation of cyclic carbonates in batch mode. Excellent selectivities of 97−100% and yields of 53−62% were obtained with tetrabutylammonium chloride supported on the silicon oxycarbides. For comparison, the catalytic performance of commonly employed silica-supported ionic liquids was investigated under the same conditions. The silica-supported species triggered the formation of a diol as a byproduct, leading to a lower selectivity of 87% and a lower yield of 48%. Ultimately, macroporous monolithic SiOC-SILPs with suitable permeability characteristics (k 1 = 10 −11 m 2 ) were produced via photopolymerization-assisted solidification templating and applied for the selective and continuous production of limonene carbonate with supercritical carbon dioxide as the reagent and sole solvent. Constant product output over 48 h without concurrent catalyst leaching was achieved.

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Section: Introductionmentioning

confidence: 99%

Silicon Oxycarbide (SiOC)-Supported Ionic Liquids: Heterogeneous Catalysts for Cyclic Carbonate Formation

Mikšovsky,

Rauchenwald,

Naghdi

et al. 2024

ACS Sustainable Chem. Eng.

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“…46,47 Lipases are frequently utilized at both academic and industrial levels, [48][49][50][51] with applications as detergents (as fat cleaning), [52][53][54][55] food and feed industries (modifying oils and fats), [56][57][58][59][60][61] fine chemistry (resolution of racemic mixtures, regio-or enantio-selective acylations, etc. ), [62][63][64][65][66][67] polymer science (production or degradation of polymeric materials), [68][69][70][71] or energy (production of biodiesel). [72][73][74][75][76][77] They have a specific catalytic feature: they can act on interfaces.…”

Section: Introductionmentioning

confidence: 99%

The effects of the chemical modification on immobilized lipase features are affected by the enzyme crowding in the support

Abellanas‐Perez,

Carballares,

Rocha‐Martin

et al. 2023

Biotechnology Progress

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In this article, we have analyzed the interactions between enzyme crowding on a given support and its chemical modification (ethylenediamine modification via the carbodiimide route and picryl sulfonic (TNBS) modification of the primary amino groups) on the enzyme activity and stability. Lipase from Thermomyces lanuginosus (TLL) and lipase B from Candida antarctica (CALB) were immobilized on octyl‐agarose beads at two very different enzyme loadings, one of them exceeding the capacity of the support, one well under this capacity. Chemical modifications of the highly loaded and lowly loaded biocatalysts gave very different results in terms of activity and stability, which could increase or decrease enzyme activity depending on the enzyme support loading. For example, both lowly loaded biocatalysts increased their activity after modification while the effect was the opposite for the highly loaded biocatalysts. Additionally, the modification with TNBS of highly loaded CALB biocatalyst increased its stability while decrease the activity.

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Hydrolases and their application in asymmetric synthesis

Sandoval

2024

Biocatalysis in Asymmetric Synthesis

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Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen

Cited by 9 publications

References 53 publications

Silicon Oxycarbide (SiOC)-Supported Ionic Liquids: Heterogeneous Catalysts for Cyclic Carbonate Formation

Silicon Oxycarbide (SiOC)-Supported Ionic Liquids: Heterogeneous Catalysts for Cyclic Carbonate Formation

The effects of the chemical modification on immobilized lipase features are affected by the enzyme crowding in the support

Hydrolases and their application in asymmetric synthesis

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